US 11,780,807 B2
Benzoselenophene, benzothiophene, and benzofuran analogs and methods of modulating the serotonin 5-HT2C receptor
David Gilles, Seattle, WA (US)
Assigned to Kuleon, LLC, Seattle, WA (US)
Filed by Kuleon, LLC, Seattle, WA (US)
Filed on Apr. 25, 2023, as Appl. No. 18/306,652.
Application 18/306,652 is a continuation of application No. PCT/US2022/040048, filed on Aug. 11, 2022.
Claims priority of provisional application 63/325,515, filed on Mar. 30, 2022.
Claims priority of provisional application 63/319,200, filed on Mar. 11, 2022.
Claims priority of provisional application 63/314,377, filed on Feb. 26, 2022.
Claims priority of provisional application 63/314,378, filed on Feb. 26, 2022.
Claims priority of provisional application 63/314,379, filed on Feb. 26, 2022.
Claims priority of provisional application 63/301,196, filed on Jan. 20, 2022.
Claims priority of provisional application 63/292,567, filed on Dec. 22, 2021.
Claims priority of provisional application 63/285,688, filed on Dec. 3, 2021.
Claims priority of provisional application 63/285,679, filed on Dec. 3, 2021.
Claims priority of provisional application 63/285,656, filed on Dec. 3, 2021.
Claims priority of provisional application 63/239,965, filed on Sep. 2, 2021.
Claims priority of provisional application 63/239,964, filed on Sep. 2, 2021.
Claims priority of provisional application 63/239,963, filed on Sep. 2, 2021.
Claims priority of provisional application 63/238,132, filed on Aug. 28, 2021.
Claims priority of provisional application 63/238,133, filed on Aug. 28, 2021.
Claims priority of provisional application 63/238,135, filed on Aug. 28, 2021.
Claims priority of provisional application 63/238,134, filed on Aug. 28, 2021.
Claims priority of provisional application 63/232,548, filed on Aug. 12, 2021.
Claims priority of provisional application 63/232,614, filed on Aug. 12, 2021.
Claims priority of provisional application 63/232,539, filed on Aug. 12, 2021.
Prior Publication US 2023/0257346 A1, Aug. 17, 2023
Int. Cl. C07D 209/04 (2006.01)
CPC C07D 209/04 (2013.01) 30 Claims
 
1. A compound of Formula I:

OG Complex Work Unit Chemistry
wherein
X and Y are each independently selected from unsubstituted C1-C8 alkyl, unsubstituted C2-C8 alkenyl, C1-C8 alkyl substituted with at least one deuterium, and C2-C8 alkenyl substituted with at least one deuterium;
W1 is selected from Se, Se(O), SeO2, S, S(O), and O;
W2 is selected from -CD2-, -(CD2)2-, -CHD-, —CH2— and —(CH2)2—;
Z4 is selected from N and CR4;
Z5 is selected from N and CR5;
Z6 is CR6;
Z7 is selected from N and CR7;
R2, R3, R3′, and R7 are each independently selected from hydrogen, deuterium, hydroxyl, —N(R9)2, —SR9, halo, optionally substituted C1-C8 alkyl, —C1-C8 alkoxy, and optionally substituted C2-C8 alkenyl, or Y is absent and R3 taken together with carbon to which it is attached and the nitrogen atom to which X is attached form a 3- to 7-membered heterocyclic ring optionally including 1 to 2 additional ring heteromoieties selected from O, S, S(O), SO2, and NR9;
R4 is selected from hydrogen, deuterium, optionally substituted C1-C8 alkyl, optionally substituted C2-C8 alkenyl, halo, hydroxyl, —N(R9)2, —SR9, —C1-C8 alkoxy, —OC(O)R8, —OC(O)OR8, —OP(O)O2(R9)2, and —OSO2R8;
R5 is selected from hydrogen, deuterium, optionally substituted C1-C8 alkyl, optionally substituted C2-C8 alkenyl, halo, hydroxyl, —N(R9)2, —SR9, —C1-C8 alkoxy, —OC(O)R8, —OC(O)OR8, —OP(O)O2(R9)2, and —OSO2R8;
R6 is selected from halo and a C1-C8 alkyl substituted with at least one halo;
R8 is selected from optionally substituted C1-C8 alkyl, optionally substituted C2-C8 alkenyl, and optionally substituted aryl;
R9 is independently selected from hydrogen, deuterium, optionally substituted C1-C8 alkyl, optionally substituted C2-C8 alkenyl, and optionally substituted aryl; and
salts, solvates, hydrates, and prodrugs thereof.